In 1929, making and distributing illegal alcohol was Detroit's No. 2 industry, behind automobiles. By the mid-20s, the city was home to more than 25,000 illegal speakeasies -- most of them controlled by the Purple Gang.

1931: Fall of the Purple Gang: the Collingwood Manor Massacre

In 1931, three members of the Purple Gang were murdered by their own after allegedly betraying gang members.

After being invited to a "peace conference" at an apartment on Collingwood Avenue in Detroit, Herman "Hymie" Paul, "Joe Sutker," and Joseph Lebowitz were gunned down at point-blank range.

As the story goes, Ray Bernstein, one of the Purples' founders, devised a plan to kill the three men for failing to pay back past-due debts. He would use Sol Levine, a friend of both groups, as an accomplice.

After buying an apartment at the Collingwood Manor Apartments, Bernstein convinced Levine that the Purples were partnering with the three men in the liquor business.

The meeting was set for Sept. 16, 1931. The men arrived and, after some conversation, Bernstein waited in the getaway car. Harry Fleisher was cued, stood up and killed all three men. Levine watched it all unfold, helplessly.

The four members of the gang, Bernstein, Keywell, Milberg and Fleisher, fled the scene, leaving Sol Levine as the only eyewitness. Police questioned Levine until he confessed to seeing the murders and telling police who did it.

After the Levine confession, police received an anonymous tip informing them where the Collingwood shooters were. Heavily armed police invaded the area, located at 2649 Calvert, and arrested Bernstein and Keywell in their pajamas. They arrested Irving Milberg the following night, after he tried fleeing the city.

In the end, Milberg, Keywell and Bernstein were convicted of first-degree murder and were sentenced to life in prison. Fleisher was never convicted in connection with the massacre.

At the time, Detroit Police Chief of Detectives, James E. McCarty, said the convictions, "broke the back of the once powerful Purple Gang, writing finis to more than five years of arrogance and terrorism."

The Collingwood Manor Massacre crippled the Purple Gang’s influence by leading to the arrests of vital members. Intra-gang rivalries, inter-gang disputes, legal convictions, and multiple homicides weakened the group. Other criminal organizations filled the voids left by the Purple Gang’s dismantled empire. The Collingwood Manor Massacre represents the primary moment that the gang’s power shifted toward decline. (DHS)